Turning Strategy into Action: The Role of Strategic Initiatives
At Regroup, one of the best parts of our work is helping companies turn their big ideas into real, actionable steps. Strategic initiatives are key to this process. They are the big bets that connect a company’s purpose and guiding principle to specific actions that drive progress. But creating good initiatives isn’t just about setting ambitious goals. It’s about focusing on what matters most and will make the biggest difference.
In this article, I’ll explain how to create strategic initiatives, using an example of a fictional retail company. Their purpose—“community-first customer care”—helped guide their planning process. Along the way, I’ll share common challenges teams face and tips to avoid them, as well as how to handle the emotions that come with making tough decisions.
Looking at the Regroup Strategy Framework, we start with Purpose, and Guiding Principle, and then clarify the Strategic Initiatives to pursue and the Tasks for each of those initiatives.
Strategic Initiatives and Tasks translate the big ideas to clear action to help the organization execute on their vision.
What Makes a Good Strategic Initiative?
Not every goal is a good strategic initiative. To be effective, an initiative needs to meet four key criteria:
It’s Connected to the Company’s Purpose
The initiative should directly support the company’s guiding principle and purpose. It should help move the company closer to its vision for the future.It Focuses on What Matters Most
The initiative should address an important challenge or opportunity that can have a big impact.It’s Big Enough
The initiative should take 18mo to 3 years to achieve. If it’s smaller than that, it’s probably a quarterly goal or actionable task.
It’s Clear and Achievable
The initiative should be well-defined, realistic, and, if possible, measurable. That said, flexibility is important too, as plans often need to adapt.
Here are some examples of strong strategic initiatives:
Improving Digital Accessibility: A fictional tech company made its products easier to use for everyone by adding accessibility features with the help of user advocates.
Going Carbon Neutral by 2030: A fictional retail company committed to reducing its carbon footprint through sustainable sourcing, renewable energy, and eco-friendly product designs.
Training for Future Jobs: A manufacturing company taught employees skills like machine learning and data science to prepare for industry changes.
Promoting Health and Nutrition: A healthcare provider partnered with local organizations to fight food insecurity and offer education on healthy eating.
Each of these initiatives is tied to a company’s mission, is high-impact, and has clear steps to measure progress.
Do Strategic Initiatives Need to Be Measurable?
This is a common question, and the answer is: not always. Some initiatives focus on setting a direction rather than achieving specific numbers. For example, our fictional retail company had a goal to improve their digital presence. While it didn’t have specific metrics at first, the team set milestones to track progress, like launching a new website or reaching a certain number of online customers.
Having at least some measurable elements—like timelines, milestones, or assigned resources—can help keep things on track. Even if you can’t measure everything, you can still set clear goals and check in regularly to adjust as needed.
Common Challenges When Creating Strategic Initiatives
Setting strategic initiatives isn’t always easy. Here are some challenges teams often face and how to overcome them:
1. Trying to Do Too Much
One big mistake we see is taking on too many initiatives at once. When everything is a priority, nothing gets the attention it deserves. Leaders may feel pressure to address every opportunity, but when everything is a priority, nothing truly is. And remember, these initiatives are big-bets, they won’t cover everything your organization does.
For example, in our fictional retail company, the leadership team wanted to improve inventory management, grow their online store, and launch a loyalty program—all at the same time. It was important to focus on just three initiatives that aligned most closely with their guiding principle of “community-first customer care.” This allowed them to make meaningful progress without spreading their resources too thin.
2. Setting Goals That Are Too Vague
Sometimes initiatives are too broad or abstract to be actionable. For example, “improving customer experience” sounds nice but isn’t clear enough to guide a team. Instead, goals like “launch a customer feedback tool” or “reduce customer response times by 20%” are easier to act on. Making the destination clear will also make it easier to define the actions and tasks to get there.
For our fictional retail client, they made sure each initiative was tied to specific actions, like hosting community events or expanding their rewards program. This gave the team clarity and focus.
3. Setting Goals That Are Too Small
These strategic initiatives are big bets that should take 18mo to 3 years to achieve. So, if your initiatives can be achieved in less time, they might be a task or milestone on the way to a larger initiative.
For our fictional retail example, a few of their initiatives were too small and and they decided to combine them together under a larger, more impactful and longer-term strategic goal.
4. Fear of Narrowing Focus
Some leaders hesitate to prioritize because they worry about missing opportunities. We often ask, “If you try to do everything, will anything truly succeed?”
In the retail example, the team initially resisted narrowing their focus. But by prioritizing customer loyalty, they were able to develop a rewards program and hold local events that deepened customer relationships.
How to Stay Focused While Aiming High
Balancing ambition with focus is one of the hardest parts of strategic planning. Many leaders want to tackle every opportunity, but trying to do it all can lead to burnout and scattered results.
Our advice: Pick a few high-impact initiatives that align with your company’s purpose.
For our fictional retail client, focusing on three initiatives helped them make real progress. They were able to:
Launch a customer rewards program.
Host regular community events to connect with their audience.
Expand their e-commerce capabilities to serve more customers.
Why Accountability Matters
A strategic initiative is only as good as the team’s commitment to following through. Clear ownership and accountability are key. We encourage our clients to designate one owner for each initiative, and to establish quarterly tasks and owners for each of those tasks, and then conduct regular check-ins to assess progress, reflect on learnings, and tackle obstacles.
For example, in our fictional retail company, each initiative had a designated owner, and the owners met with the executive team quarterly to review progress. These check-ins helped surface issues early—like a lack of resources—and allowed the team to adjust plans before bigger problems arose.
Regular accountability creates a culture of commitment and transparency. When each leader is responsible for tracking and reporting progress, it reinforces that the strategic plan is not just an idea on paper but an active, evolving process. This lightweight accountability process helped our client celebrate small wins and maintain momentum over time, which can be motivating for the team, especially when faced with challenges that test resilience and patience.
Adapting Initiatives as Things Change
Strategic initiatives are not set in stone. As the business environment shifts, initiatives may need to evolve. This flexibility isn’t a sign of failure—it’s a sign of responsiveness and growth.
For instance, after a year, our fictional retail company realized that rapid changes in online shopping meant they needed to focus more on e-commerce improvements than on in-store changes. By revisiting and adjusting their initiatives, they stayed aligned with customer needs and market trends.
We recommend reviewing strategic initiatives at least once a year to ensure they’re still relevant and high-priority.
Dealing with the Emotional Side of Setting Strategic Priorities
Strategic planning can stir up emotions, especially when it involves tough decisions like letting go of certain goals or reallocating resources. Leaders may feel disappointed or worried about leaving opportunities untapped. Teams may resist changes, especially if they’re attached to projects that don’t make the final cut.
In our fictional retail client’s case, narrowing focus meant putting aside some ideas that team members were passionate about. Open communication and connecting decisions to their purpose—“community-first customer care”—helped the team accept the changes and stay motivated.
The Benefits of Strong Strategic Initiatives
When done well, strategic initiatives provide more than just a roadmap—they create alignment, purpose, and momentum. Teams feel energized when they know their work directly supports the company’s mission. Leaders gain confidence as they see progress toward big-picture goals.
Whether it’s launching a new product, growing customer loyalty, or investing in sustainability, strong initiatives turn ideas into action and drive meaningful results.
If your team could use help defining and achieving its strategic initiatives, reach out to Regroup. We’d love to help you turn your vision into reality.
Questions for Reflection:
Are your strategic initiatives focused on high-impact areas aligned with your purpose and guiding principles?
Reflect on whether your initiatives directly support your mission and address the most pressing challenges.Do you have accountability measures in place to track each initiative’s progress?
Clear ownership and accountability can help keep your initiatives on track and ensure alignment across teams.Have you revisited your strategic initiatives recently?
If your initiatives haven’t been reviewed in the past year, it might be time to assess their relevance and make adjustments where needed.
If this article sparks ideas for your own organizational strategy, please reach out and say hello. We’d love to hear from you!
